Holiday rentals in Pineland

Island Paradise - Hot tub, Bikes & Ocean fishing

Welcome to The Clubhouse – Your Private Island Escape Experience laid-back luxury on the serene Florida island 🏝️ just two blocks from the marina. This beautifully appointed retreat features an outdoor kitchen, fire pit, hot tub, and elegant indoor-outdoor living. Cruise the island on provided bikes, kids get to stay the new designer bunk space. Perfect for boating, fishing, or simply soaking in the sun. Refined comfort meets coastal charm — reserve your stay today, your island retreat awaits!

Garden Cottage - Tiny House

PLEASE NOTE: The cottage is separate from our house and living quarters. The bathroom is in the back of the main house, just a few steps from the cottage, private and not shared with anyone. We take special precautions to thoroughly clean and disinfect the bedroom and bathroom after each guest. You’ll love our place because of the location, the ambiance, the outdoor space, and the neighborhood. We have a dog and a cat. Our place is good for couples, solo adventurers, and business travelers.

Romantic Getaway “Waterside” Dockage~Canal front

Also available: airbnb.com/h/aframeausable Minutes to open water and Jug Creek Marina! Wait till you see this freshly updated cottage! Bring your boat, or rent one nearby. There is a dock available here. Tarpon capital of the world, and Charlotte Harbor moments away! Boca Grande, Cayo Costa, Useppa, North Captiva, Sanibel and Cabbage Key, etc. a short boat ride away! The golf carts/kayaks/boats/bikes are available to rent at local resources! Jug Creek Marina is steps away with food & music!

Boaters Paradise: Private 1/1 with FREE parking!

Escape to your own peaceful slice of Southwest Florida! This cozy 1-bedroom offers everything you need for a comfortable, laid-back stay — just 1 mile from the famous Matlacha Bridge, known as “The Fishingest Bridge in America!” Perfect for solo travelers, couples, or boaters, this unit features a full kitchenette, private bath, and comfortable living area. You’ll also have access to FREE onsite parking for boats, trailers, RV's, etc. and be close to three public boat ramps within a mile.

Susie's Old Florida Cottage

Explore Pine Island & the Florida Gulf Coast from this retro 2-room cottage set in a pretty back yard. 45 min from Ft. Myers Beach/Sanibel. Wi-fi, A/C, kitchen, v small bathroom w/shower, 1 bedroom, cozy private deck, screened lanai. Perfect for 1 or 2. Avoid the motel feel & enjoy your privacy. Discounts for weekly/monthly bookings. No beaches on PIne Island, but enjoy kayaking, birding, biking, tennis, boating, & fishing. May 2023: Pine Island is still recovering from Hurricane Ian.

The Bokeelia Cottage

This tiny home is perfect for those seeking a peaceful retreat from every day life! Located in the quiet little fishing town of Bokeelia. Minutes from several boat ramps, restaurants, and the Bokeelia fishing pier. Take the local ferry out to the outside islands like Cayo Costa, Captiva, or Cabage Key or enjoy your time on the beautiful front porch overlooking your own private pond. Catch and release is always welcomed and don't be surprised if you see wild peacocks passing through!

Matlacha Paradise! NEW Waterfront Home-Free Kayak

Matlacha is for LOVERS! Lovers of relaxation, fishing, art, friends, social scenes and enjoying Life in a beautiful location ON THE WATER! Matlacha had damage from Ian. Our new home - none. You can still walk to great restaurants, shops and the fishing bridge. Enjoy the water in Matlacha & the Barrier Islands. Use our 1 person kayak for fun or fishing from our 8'X22' FUN & SUN deck docked in the back canal with picnic table & loungers. Relax, sun, grill and fish.

Peaceful Lakeview Retreat / Screened Porch & Bikes

Escape to a peaceful lakeview retreat on Pine Island. Relax on the breezy screened porch, unwind in the cozy living room, and enjoy two serene bedrooms with smart TVs and comfortable bedding. The home features modern bathrooms, a fully stocked kitchen, fast Wi-Fi, and in-unit laundry for convenience. Pet-friendly and close to trails, marinas, and seafood spots — perfect for birdwatching, biking, fishing, or simply soaking up the island’s quiet charm and natural beauty.

Pine Island Pelican Suite: privacy, pool, gardens

Welcome to the Pelican Suite! Secure, private entrance, king bed, living area with kitchen and patio. This suite is separate from the upstairs main house. Adults only. King bed, ensuite private bathroom with shower; AC. WiFi, cable, TV. Exclusive use of screened guest lanai - kitchen, fridge, BBQ, gardens, secluded heated pool. Free parking. The Pelican Suite is ideal for a relaxing no-stress break in the sun!

Sunny Island Cottage w/ Large Patio

This charming one bed/one bath home is very spacious, tiled throughout, and includes a large privately fenced in back patio to enjoy the Florida weather. This home is outfitted with mini split AC, newly renovated bathroom, and a washer and dryer inside for your convenience. This home is located near two public marinas and boat, so you are welcome to park your boat trailer on our spacious property

Paradise Found! - 3/2 Pool Home

Escape to our Tropical Oasis in Bokeelia, Pine Island, Florida! This 3-bed pool home offers comfort and style. Enjoy a private pool, lush surroundings, and amenities galore. Minutes from SWFL's best beaches, Cape Coral, Fort Myers, Matlacha, and Pine Island's restaurants and shops. Book now for a perfect blend of relaxation and adventure!

Breakaway in Bokeelia!

Forget your worries in this spacious and serene space. Enjoy either family/friend time or alone time in this well thought out floor plan. The 1/3 of an acre also allows for plenty of room to take in the laid back island vibe. Jug Creek marina and Lavender's Landing public boat ramp just minutes away.